NO319323B1 - Reactive systems consisting of a polyisocyanate component, at least one organic polyamine, and optionally, oxirane group-containing compounds and their use. - Google Patents
Reactive systems consisting of a polyisocyanate component, at least one organic polyamine, and optionally, oxirane group-containing compounds and their use. Download PDFInfo
- Publication number
- NO319323B1 NO319323B1 NO19991766A NO991766A NO319323B1 NO 319323 B1 NO319323 B1 NO 319323B1 NO 19991766 A NO19991766 A NO 19991766A NO 991766 A NO991766 A NO 991766A NO 319323 B1 NO319323 B1 NO 319323B1
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- Norway
- Prior art keywords
- groups
- component
- reactive systems
- molecular weight
- systems according
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- 239000005056 polyisocyanate Substances 0.000 title claims abstract description 34
- 229920001228 polyisocyanate Polymers 0.000 title claims abstract description 34
- 150000001875 compounds Chemical class 0.000 title claims abstract description 20
- 229920000768 polyamine Polymers 0.000 title claims abstract description 19
- 125000000466 oxiranyl group Chemical group 0.000 title abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 23
- 239000013032 Hydrocarbon resin Substances 0.000 claims abstract description 21
- 229920006270 hydrocarbon resin Polymers 0.000 claims abstract description 21
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims abstract description 19
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 13
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 7
- 239000002981 blocking agent Substances 0.000 claims abstract description 6
- 238000004519 manufacturing process Methods 0.000 claims description 23
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 239000004033 plastic Substances 0.000 claims description 12
- 229920003023 plastic Polymers 0.000 claims description 12
- 239000003054 catalyst Substances 0.000 claims description 11
- 238000000576 coating method Methods 0.000 claims description 10
- 230000001747 exhibiting effect Effects 0.000 claims description 8
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 6
- 239000000853 adhesive Substances 0.000 claims description 4
- 230000001070 adhesive effect Effects 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 239000011248 coating agent Substances 0.000 claims description 4
- 238000000465 moulding Methods 0.000 claims description 4
- 238000007789 sealing Methods 0.000 claims description 4
- 239000000654 additive Substances 0.000 claims description 3
- 238000005516 engineering process Methods 0.000 claims description 3
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 2
- 150000004985 diamines Chemical class 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 239000004850 liquid epoxy resins (LERs) Substances 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- 125000004185 ester group Chemical group 0.000 claims 1
- 230000002441 reversible effect Effects 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 34
- 239000012948 isocyanate Substances 0.000 description 17
- 150000002513 isocyanates Chemical class 0.000 description 17
- -1 isocyanaurate Chemical compound 0.000 description 14
- 229920005862 polyol Polymers 0.000 description 11
- 150000003077 polyols Chemical class 0.000 description 11
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- 229920000647 polyepoxide Polymers 0.000 description 9
- 239000013065 commercial product Substances 0.000 description 8
- 239000003822 epoxy resin Substances 0.000 description 8
- 229920000570 polyether Polymers 0.000 description 8
- 239000004721 Polyphenylene oxide Substances 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 150000002009 diols Chemical class 0.000 description 7
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 6
- IGSBHTZEJMPDSZ-UHFFFAOYSA-N 4-[(4-amino-3-methylcyclohexyl)methyl]-2-methylcyclohexan-1-amine Chemical compound C1CC(N)C(C)CC1CC1CC(C)C(N)CC1 IGSBHTZEJMPDSZ-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 150000001409 amidines Chemical class 0.000 description 6
- JQZRVMZHTADUSY-UHFFFAOYSA-L di(octanoyloxy)tin Chemical compound [Sn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O JQZRVMZHTADUSY-UHFFFAOYSA-L 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 238000002329 infrared spectrum Methods 0.000 description 5
- 239000004593 Epoxy Substances 0.000 description 4
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- 230000000903 blocking effect Effects 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- KUBDPQJOLOUJRM-UHFFFAOYSA-N 2-(chloromethyl)oxirane;4-[2-(4-hydroxyphenyl)propan-2-yl]phenol Chemical compound ClCC1CO1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 KUBDPQJOLOUJRM-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CCTFMNIEFHGTDU-UHFFFAOYSA-N 3-methoxypropyl acetate Chemical compound COCCCOC(C)=O CCTFMNIEFHGTDU-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000005058 Isophorone diisocyanate Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 150000002118 epoxides Chemical group 0.000 description 3
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 3
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 3
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000004814 polyurethane Substances 0.000 description 3
- 229920002635 polyurethane Polymers 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 3
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 3
- XMGQYMWWDOXHJM-JTQLQIEISA-N (+)-α-limonene Chemical compound CC(=C)[C@@H]1CCC(C)=CC1 XMGQYMWWDOXHJM-JTQLQIEISA-N 0.000 description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
- DZIHTWJGPDVSGE-UHFFFAOYSA-N 4-[(4-aminocyclohexyl)methyl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1CC1CCC(N)CC1 DZIHTWJGPDVSGE-UHFFFAOYSA-N 0.000 description 2
- CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000001361 adipic acid Substances 0.000 description 2
- 235000011037 adipic acid Nutrition 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000007046 ethoxylation reaction Methods 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 235000013312 flour Nutrition 0.000 description 2
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 150000003951 lactams Chemical class 0.000 description 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 2
- KPADFPAILITQBG-UHFFFAOYSA-N non-4-ene Chemical compound CCCCC=CCCC KPADFPAILITQBG-UHFFFAOYSA-N 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 229920006122 polyamide resin Polymers 0.000 description 2
- 238000006068 polycondensation reaction Methods 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 150000003505 terpenes Chemical class 0.000 description 2
- 235000007586 terpenes Nutrition 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- GRWFGVWFFZKLTI-IUCAKERBSA-N (-)-α-pinene Chemical compound CC1=CC[C@@H]2C(C)(C)[C@H]1C2 GRWFGVWFFZKLTI-IUCAKERBSA-N 0.000 description 1
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical group C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
- PCHXZXKMYCGVFA-UHFFFAOYSA-N 1,3-diazetidine-2,4-dione Chemical compound O=C1NC(=O)N1 PCHXZXKMYCGVFA-UHFFFAOYSA-N 0.000 description 1
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- NFDXQGNDWIPXQL-UHFFFAOYSA-N 1-cyclooctyldiazocane Chemical compound C1CCCCCCC1N1NCCCCCC1 NFDXQGNDWIPXQL-UHFFFAOYSA-N 0.000 description 1
- LRTOHSLOFCWHRF-UHFFFAOYSA-N 1-methyl-1h-indene Chemical compound C1=CC=C2C(C)C=CC2=C1 LRTOHSLOFCWHRF-UHFFFAOYSA-N 0.000 description 1
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- HCKPQGBXPQNMKU-UHFFFAOYSA-N 2,3-bis[(dimethylamino)methyl]phenol Chemical compound CN(C)CC1=CC=CC(O)=C1CN(C)C HCKPQGBXPQNMKU-UHFFFAOYSA-N 0.000 description 1
- DPQHRXRAZHNGRU-UHFFFAOYSA-N 2,4,4-trimethylhexane-1,6-diamine Chemical compound NCC(C)CC(C)(C)CCN DPQHRXRAZHNGRU-UHFFFAOYSA-N 0.000 description 1
- AHDSRXYHVZECER-UHFFFAOYSA-N 2,4,6-tris[(dimethylamino)methyl]phenol Chemical compound CN(C)CC1=CC(CN(C)C)=C(O)C(CN(C)C)=C1 AHDSRXYHVZECER-UHFFFAOYSA-N 0.000 description 1
- YSUQLAYJZDEMOT-UHFFFAOYSA-N 2-(butoxymethyl)oxirane Chemical compound CCCCOCC1CO1 YSUQLAYJZDEMOT-UHFFFAOYSA-N 0.000 description 1
- RWLALWYNXFYRGW-UHFFFAOYSA-N 2-Ethyl-1,3-hexanediol Chemical compound CCCC(O)C(CC)CO RWLALWYNXFYRGW-UHFFFAOYSA-N 0.000 description 1
- FZZMTSNZRBFGGU-UHFFFAOYSA-N 2-chloro-7-fluoroquinazolin-4-amine Chemical compound FC1=CC=C2C(N)=NC(Cl)=NC2=C1 FZZMTSNZRBFGGU-UHFFFAOYSA-N 0.000 description 1
- FEJIGNDKURQIRD-UHFFFAOYSA-N 2-methyl-1,2,3,4-tetrahydropyrimidine Chemical group CC1NCC=CN1 FEJIGNDKURQIRD-UHFFFAOYSA-N 0.000 description 1
- RREANTFLPGEWEN-MBLPBCRHSA-N 7-[4-[[(3z)-3-[4-amino-5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidin-2-yl]imino-5-fluoro-2-oxoindol-1-yl]methyl]piperazin-1-yl]-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(\N=C/3C4=CC(F)=CC=C4N(CN4CCN(CC4)C=4C(=CC=5C(=O)C(C(O)=O)=CN(C=5C=4)C4CC4)F)C\3=O)=NC=2)N)=C1 RREANTFLPGEWEN-MBLPBCRHSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
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- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
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- 239000005700 Putrescine Substances 0.000 description 1
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 1
- 241000779819 Syncarpia glomulifera Species 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- KXBFLNPZHXDQLV-UHFFFAOYSA-N [cyclohexyl(diisocyanato)methyl]cyclohexane Chemical compound C1CCCCC1C(N=C=O)(N=C=O)C1CCCCC1 KXBFLNPZHXDQLV-UHFFFAOYSA-N 0.000 description 1
- LDZDQDDROJXUBO-UHFFFAOYSA-N acetic acid;dibutyltin Chemical compound CC(O)=O.CC(O)=O.CCCC[Sn]CCCC LDZDQDDROJXUBO-UHFFFAOYSA-N 0.000 description 1
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- 230000002411 adverse Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
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- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 239000010425 asbestos Substances 0.000 description 1
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- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- HIFVAOIJYDXIJG-UHFFFAOYSA-N benzylbenzene;isocyanic acid Chemical class N=C=O.N=C=O.C=1C=CC=CC=1CC1=CC=CC=C1 HIFVAOIJYDXIJG-UHFFFAOYSA-N 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 1
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- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 1
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- 239000006227 byproduct Substances 0.000 description 1
- 238000010538 cationic polymerization reaction Methods 0.000 description 1
- 239000003251 chemically resistant material Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 239000007799 cork Substances 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- IFDVQVHZEKPUSC-UHFFFAOYSA-N cyclohex-3-ene-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCC=CC1C(O)=O IFDVQVHZEKPUSC-UHFFFAOYSA-N 0.000 description 1
- VKIRRGRTJUUZHS-UHFFFAOYSA-N cyclohexane-1,4-diamine Chemical compound NC1CCC(N)CC1 VKIRRGRTJUUZHS-UHFFFAOYSA-N 0.000 description 1
- ZQWRZCZEOLZBQF-UHFFFAOYSA-N cyclopentane-1,3-diamine Chemical compound NC1CCC(N)C1 ZQWRZCZEOLZBQF-UHFFFAOYSA-N 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000012973 diazabicyclooctane Substances 0.000 description 1
- WCRDXYSYPCEIAK-UHFFFAOYSA-N dibutylstannane Chemical compound CCCC[SnH2]CCCC WCRDXYSYPCEIAK-UHFFFAOYSA-N 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 1
- 239000013013 elastic material Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 1
- DMNYJSMNRDYEOT-UHFFFAOYSA-N n,n,n'-trimethylmethanimidamide Chemical compound CN=CN(C)C DMNYJSMNRDYEOT-UHFFFAOYSA-N 0.000 description 1
- SRPCLECGIYMIMN-UHFFFAOYSA-N n,n-dimethyl-n'-phenylmethanimidamide Chemical compound CN(C)C=NC1=CC=CC=C1 SRPCLECGIYMIMN-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical class CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 125000005474 octanoate group Chemical group 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000001739 pinus spp. Substances 0.000 description 1
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920005906 polyester polyol Polymers 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920006295 polythiol Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- ZNZJJSYHZBXQSM-UHFFFAOYSA-N propane-2,2-diamine Chemical compound CC(C)(N)N ZNZJJSYHZBXQSM-UHFFFAOYSA-N 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000007779 soft material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 1
- 229950006389 thiodiglycol Drugs 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 229940036248 turpentine Drugs 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- GKXVJHDEWHKBFH-UHFFFAOYSA-N xylylenediamine group Chemical group C=1(C(=CC=CC1)CN)CN GKXVJHDEWHKBFH-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
- C08L75/04—Polyurethanes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
- C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation step
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/64—Macromolecular compounds not provided for by groups C08G18/42 - C08G18/63
- C08G18/6476—Bituminous materials, e.g. asphalt, coal tar, pitch; derivatives thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Civil Engineering (AREA)
- Structural Engineering (AREA)
- Polyurethanes Or Polyureas (AREA)
- Sealing Material Composition (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Application Of Or Painting With Fluid Materials (AREA)
- Paints Or Removers (AREA)
Abstract
Description
Foreliggende oppfinnelse vedrører nye reaktivsystemer på basis av en polyisocyanatkomponent med blokkerte isocyanatgrupper og en reaktivkomponent med primære aminogrupper samt eventuelt en ytterligere reaktiv komponent med oksirangmpper, samt anvendelsen av disse reaktivsystemene for fremstilling av belegg, klebestoffer, tetningsmasser, støpemasser eller formdeler. The present invention relates to new reactive systems on the basis of a polyisocyanate component with blocked isocyanate groups and a reactive component with primary amino groups as well as possibly a further reactive component with oxirangamps, as well as the use of these reactive systems for the production of coatings, adhesives, sealing compounds, molding compounds or molded parts.
Reaktivsystemer på basis av blokkerte isocyanater og polyaminer er kjente i stort antall. DE-A 16 44 813 beskriver fremstillingen av belegningsmasser på asis av ketoksim-blokkerte polyisocyanater og organiske polyaminer. Disse systemene herder ekstremt langsomt ved romtemperatur og nødvendiggjør for utherding som regel temperaturer over 120°C. For det ene er denne temperaturbehandlingen i mange tilfeller ikke mulig, og for det andre viser systemene ved denne temperaturbehandlingen tendens til blære-dannelse, slik at de bare kan påføres i tynne sjikt. Reactive systems based on blocked isocyanates and polyamines are known in large numbers. DE-A 16 44 813 describes the preparation of coating materials on the basis of ketoxime-blocked polyisocyanates and organic polyamines. These systems cure extremely slowly at room temperature and generally require temperatures above 120°C for curing. Firstly, this temperature treatment is not possible in many cases, and secondly, the systems with this temperature treatment show a tendency to blister, so that they can only be applied in thin layers.
DE-A 21 31 299 beskriver ved varmeinnvirkning herdbare blandinger av en polyisocyanatkomponent med kaprolaktam-blokkerte isocyanatgrupper og cykloalifatiske polyaminer. Systemene i denne publikasjonen oppviser en god lagringsstabilitet og egner seg for fremstilling av tykke besjiktninger med et høyt mekanisk egenskapsnivå. Ulempen ved disse systemene ligger imidlertid i de høye reaksjonstemperaturene på ca. 160°C, som er påkrvet for utherding. DE-A 21 31 299 describes heat-curable mixtures of a polyisocyanate component with caprolactam-blocked isocyanate groups and cycloaliphatic polyamines. The systems in this publication show good storage stability and are suitable for the production of thick coatings with a high level of mechanical properties. The disadvantage of these systems, however, lies in the high reaction temperatures of approx. 160°C, which is required for curing.
DE-A 39 22 767 beskriver varmeherdbare blandinger på basis av med sekundære mono-aminer blokkerte polyisocyanater og organiske polyaminer. Systemene ifølge denne publikajsonen viser et godt forhold mellom bearbeidelsestid på den ene siden og lav herdetemperatur på den annen side. Problematisk ved systemene ifølge denne publikasjonen er imidlertid avspaltningen av blokkeringsmidlet, som fører til en luktbelastning. Dessuten lar systemene ifølge DE-A 39 22 767 seg ikke anvende for fremstilling av romtemperaturherdende besjiktninger, idet herdehastigheten er for lav og ifølge nåværende viten ikke lar seg akselerere katalytisk. DE-A 39 22 767 describes thermosetting mixtures based on polyisocyanates blocked with secondary monoamines and organic polyamines. The systems according to this public zone show a good relationship between processing time on the one hand and low curing temperature on the other. However, the problem with the systems according to this publication is the separation of the blocking agent, which leads to an odor burden. Moreover, the systems according to DE-A 39 22 767 cannot be used for the production of room-temperature curing coatings, as the curing speed is too low and, according to current knowledge, cannot be accelerated catalytically.
DE-A 21 52 606 beskriver reaktivsystemer på basis av alkylfenol-blokkerte polyisocyanater og polyaminer, som eventuelt også kan utherdes i kombinasjon med epoksydharpikser. Også disse reaktivsystemene er beheftet med noen anvendelsestekniske ulemper: For det ene er reaktiviteten så høy at som regel bare en påføring ved romtemperatur kommer på tale, ved relativt korte bearbeidelsestider. For det andre har det frisatte blokkeringsmidlet en forholdsvis lav molekylvekt, slik at det med tiden damper av fra belegget, hvilket kan føre til vedhengsproblemer, og nivået av de mekaniske egenskapene kan påvirkes i ugunstig retning. DE-A 21 52 606 describes reactive systems based on alkylphenol-blocked polyisocyanates and polyamines, which can optionally also be cured in combination with epoxy resins. These reactive systems are also subject to some application-technical disadvantages: Firstly, the reactivity is so high that, as a rule, only an application at room temperature is possible, with relatively short processing times. Secondly, the released blocking agent has a relatively low molecular weight, so that it evaporates from the coating over time, which can lead to adhesion problems, and the level of the mechanical properties can be adversely affected.
Følgelig var den oppgaven som lå til grunn for oppfinnelsen å tilveiebringe reaktivsystemer på basis av blokkerte polyisocyanater og polyaminer som ikke er beheftet med ulempene ved systemene ifølge teknikkens stand. Consequently, the task underlying the invention was to provide reactive systems based on blocked polyisocyanates and polyamines which are not affected by the disadvantages of the systems according to the state of the art.
Gjenstand for oppfinnelsen er reaktivsystemer bestående av Subject matter of the invention are reactive systems consisting of
A) en polyisocyanatkomponent, bestående av minst ett organisk polyisocyanat med reversibelt blokkerte isocyanatgrupper, A) a polyisocyanate component, consisting of at least one organic polyisocyanate with reversibly blocked isocyanate groups,
B) minst ett organisk polyamin med minst to primære aminogrupper, B) at least one organic polyamine with at least two primary amino groups,
samt eventuelt as well as possibly
C) forbindelser som oppviser oksirangmpper, C) compounds exhibiting oxirange mps,
kjennetegnt ved at komponent A) består av minst ett polyisocyanat av molekylvektområde (uten innbefatning av blokkeringsmidlet) på 168 til 25.000, hvis isocyanatgrupper er reversibelt blokkert ved reaksjon med minst én hydrokarbonharpiks som oppviser fenoliske OH-grupper. characterized in that component A) consists of at least one polyisocyanate of molecular weight range (not including the blocking agent) of 168 to 25,000, whose isocyanate groups are reversibly blocked by reaction with at least one hydrocarbon resin exhibiting phenolic OH groups.
Gjenstand for oppfinnelsen er også anvendelsen av disse reaktivsystemene, eventuelt i kombinasjon med de innenfor plast- og belegningsteknologien vanlige katalysatorene, hjelpe- og tilsatsstoffene for fremstilling av belegg, klebestoffer, tetningsmasser, støpe-masser eller formdeler. The subject of the invention is also the use of these reactive systems, possibly in combination with the catalysts, auxiliaries and additives common in plastics and coating technology for the production of coatings, adhesives, sealing compounds, molding compounds or molded parts.
Til grunn for oppfinnelsen ligger den overraskende observasjonen at de blokkerte polyisocyanatene ifølge oppfinnelsen, sammenlignet med alkylfenol-blokkerte polyisocyanater ifølge teknikkens stand, oppviser en tydelig redusert reaktivitet overfor polyaminer. The invention is based on the surprising observation that the blocked polyisocyanates according to the invention, compared to alkylphenol-blocked polyisocyanates according to the state of the art, show a clearly reduced reactivity towards polyamines.
Fremstillingen av de ifølge oppfinnelsen som komponent A) egnede polyisocyanatene med reversibelt blokkerte isocyanatgrupper foregår ved omsetning av organiske polyisocyanater av den nedenfor angitte typen ved temperaturer på 40°C til 150°C, fortrinnsvis ved 50°C til 100°C, med de nedenfor nærmere angitte hydrokarbonharpiksene som oppviser fenoliske OH-grupper. Mengden av den ved blokkeringsreaksjonen anvendte hydrokarbonharpiksen som oppviser fenoliske OH-grupper, bør minst være ekvivalent med mengden av NCO-grupper som skal blokkeres. Ofte er et lite overskudd av blokkeringsmiddel hensiktsmessig for å sikre en fullstendig reaksjon av alle isocyanatgrupper. Som regel utgjør overskuddet ikke mer enn 20 mol-%, fortrinnsvis ikke mer enn 15 mol-%, og spesielt foretrukket ikke mer enn 10 mol-%, relativt til isocyanatgruppene som skal blokkeres. The production of the polyisocyanates suitable according to the invention as component A) with reversibly blocked isocyanate groups takes place by reacting organic polyisocyanates of the type specified below at temperatures of 40°C to 150°C, preferably at 50°C to 100°C, with the following more specifically the hydrocarbon resins exhibiting phenolic OH groups. The amount of the hydrocarbon resin used in the blocking reaction which exhibits phenolic OH groups should be at least equivalent to the amount of NCO groups to be blocked. Often a small excess of blocking agent is appropriate to ensure a complete reaction of all isocyanate groups. As a rule, the excess amounts to no more than 20 mol%, preferably no more than 15 mol%, and particularly preferably no more than 10 mol%, relative to the isocyanate groups to be blocked.
Blokkeringsreaksjonen gjennomføres fortrinnsvis under medanvendelse av katalysatorer som i og for seg er kjente fra polyuretankjemien, som eksempelvis metallorganiske forbindelser som tinn(II)oktoat, dibutyltinn(II)diacetat, dibutyltinn(U)dilaurat eller tertiære aminer samt trietylamin eller diazabicyklooktan. Blokkeringsreaksjonen kan eventuelt gjennomføres i nærvær av inerte oppløsningsmidler som de nedenfor som eksempler nevnte typene. The blocking reaction is preferably carried out with the co-use of catalysts which are known per se from polyurethane chemistry, such as organometallic compounds such as tin(II) octoate, dibutyltin(II) diacetate, dibutyltin(U) dilaurate or tertiary amines as well as triethylamine or diazabicyclooctane. The blocking reaction can optionally be carried out in the presence of inert solvents such as the types mentioned below as examples.
For fremstilling av de blokkerte polyisocyanatene A) egnede utgangspolyisocyanater er hvilke som helst organiske polyisocyanater eller polyisocyanatblandinger med en (midlere), fra isocyanatinnhold og funksjonalitet bestemt, molekylvekt på 168 til 25.000, fortrinnsvis 1000 til 12.000. Egnede utgangspolyisocyanater er de fra polyuretankjemien i og for seg kjente isocyanatene, som heksametylendiisocyanat, isoforondiisocyanat, dicykloheksylmetandiisocyanat, de isomere difenylmetandiisocyanatene samt deres høyere homologer, slik de oppstår ved fosgenering av anilin/formaldehyd-kondensasjonsprodukter, 2,4- og 2,6-toluylendiisocyanat samt deres tekniske blandinger. Likeledes egnede er i og for seg kjente følgeproduktene av de nevnte isocyanatene med biuret-, isocyanaurat-, uretdion- og/eller uretanstruktur. For the production of the blocked polyisocyanates A) suitable starting polyisocyanates are any organic polyisocyanates or polyisocyanate mixtures with a molecular weight of 168 to 25,000, preferably 1,000 to 12,000, determined from the isocyanate content and functionality. Suitable starting polyisocyanates are the isocyanates known per se from polyurethane chemistry, such as hexamethylene diisocyanate, isophorone diisocyanate, dicyclohexylmethane diisocyanate, the isomeric diphenylmethane diisocyanates as well as their higher homologues, as they arise from phosgenation of aniline/formaldehyde condensation products, 2,4- and 2,6-toluylene diisocyanate as well as their technical mixtures. The by-products of the aforementioned isocyanates with a biuret, isocyanaurate, uretdione and/or urethane structure are also suitable in and of themselves.
Fortrinnsvis dreier det seg ved utgangspolyisocyanatene om prepolymerer som oppviser isocyanatgrupper, slik de kan oppnås ved omsetning av lavere- eller høyeremolekylære Preferably, the starting polyisocyanates are prepolymers that exhibit isocyanate groups, as they can be obtained by reacting lower or higher molecular
polyhydroksylforbindelser med overskuddsmengder av de ovenfor nevnte di- eller polyisocyanatene, eller også med et stort overskudd av de nevnte di- og polyisocyanatene og etterfølgende fjernelse av det overskytende polyisocyanatet, f.eks. ved tynnsjiktsdestilla-sjon. Fremstillingen av prepolymerene foregår generelt ved 40 til 140°C, eventuelt under samtidig anvendelse av egnede katalysatorer av den ovenfor allerede nevnte typen. polyhydroxyl compounds with excess amounts of the above-mentioned di- or polyisocyanates, or also with a large excess of the mentioned di- and polyisocyanates and subsequent removal of the excess polyisocyanate, e.g. by thin layer distillation. The production of the prepolymers generally takes place at 40 to 140°C, possibly with the simultaneous use of suitable catalysts of the type already mentioned above.
For fremstilling av slike polymerer egner seg lavmolekylære polyhydroksylforbindelser av molekylvektområde 62 til 299, som eksempelvis etylenglykol, propylenglykol-1,3-og butandiol-1,4, heksandiol-1,6, neopentylglykol, 2-etylheksandiol-l,3, glyserol, trimetylolpropan, pentaerytritt, lavmolekylære estere av slike polyoler med dikarboksyl-syrer av den nedenfor angitte typen som oppviser hydroksylgrupper, eller lavmolekylære etoksylerings- eller propoksyleringsprodukter av slike enkle polyoler, eller hvilke som helst blandinger av slike modifiserte eller ikke-modifiserte alkoholer. For the production of such polymers, low molecular weight polyhydroxyl compounds with a molecular weight range of 62 to 299 are suitable, such as ethylene glycol, propylene glycol-1,3- and butanediol-1,4, hexanediol-1,6, neopentyl glycol, 2-ethylhexanediol-1,3, glycerol, trimethylolpropane, pentaerythritol, low molecular weight esters of such polyols with dicarboxylic acids of the type indicated below which exhibit hydroxyl groups, or low molecular weight ethoxylation or propoxylation products of such simple polyols, or any mixtures of such modified or unmodified alcohols.
Fortrinnsvis anvendes imidlertid for fremstilling av prepolymerene høyeremolekylære hydroksylforbindelser av molekylvektområde 300 til 20.000, fortrinnsvis 1000 til 8000, av den fra polyuretankjemien i og for seg kjente typen. Høyeremolekylære polyhydroksylforbindelser for fremstilling av prepolymerer er eksempelvis polyester-polyolene som stemmer overens med de angitte angivelsene på basis av lavmolekylære enkle alkoholer av den allerede eksempelvis nevnte typen og flerverdige karboksylsyrer, som eksempelvis adipinsyre, sebacinsyre, ftalsyre, isoftalsyre, tetrahydroftalsyre, heksahydroftalsyre, maleinsyre, anhydridene av slike syrer eller hvilke som helst blandinger av slike syrer, henholdsvis anhydrider. Også polylaktoner, som oppviser hydroksylgrupper av den ovenfor angitte typen, spesielt poly-s-kaprolaktoner, er egnede for fremstilling av prepolymerene, henholdsvis semi-prepolymerene. However, higher molecular weight hydroxyl compounds of the molecular weight range 300 to 20,000, preferably 1,000 to 8,000, of the type known per se from polyurethane chemistry, are preferably used for the production of the prepolymers. Higher molecular weight polyhydroxyl compounds for the production of prepolymers are, for example, the polyester polyols which comply with the given specifications on the basis of low molecular weight simple alcohols of the already mentioned type and polyhydric carboxylic acids, such as for example adipic acid, sebacic acid, phthalic acid, isophthalic acid, tetrahydrophthalic acid, hexahydrophthalic acid, maleic acid, the anhydrides of such acids or any mixtures of such acids, respectively anhydrides. Also polylactones, which exhibit hydroxyl groups of the type indicated above, especially poly-s-caprolactones, are suitable for producing the prepolymers, respectively the semi-prepolymers.
For fremstilling av prepolymerene som oppviser isocyanatgrupper er likeledes godt egnede polyeterpolyolene tilsvarende de ovenfor angitte betraktningene, som på i og for seg kjent måte er tilgjengelige ved alkoksylering av egnede startermolekyler. For the production of the prepolymers which exhibit isocyanate groups, the polyether polyols corresponding to the above-mentioned considerations, which are available in a manner known per se by alkoxylation of suitable starter molecules, are likewise well suited.
Egnede startermolekyler er eksempelvis de ovenfor allerede nevnte enkle polyolene, vann, organiske polyaminer med minst to N-H-bindinger, eller hvilke som helst blandinger av slike startermolekyler. For alkoksyleringsreaksjonen egnede alkylen-oksyder er spesielt etylenoksyd og/eller propylenoksyd, som kan anvendes i en hvilken som helst rekkefølge, eller også i blanding, ved alkoksyleringsreaksjonen. Suitable starter molecules are, for example, the simple polyols already mentioned above, water, organic polyamines with at least two N-H bonds, or any mixtures of such starter molecules. Alkylene oxides suitable for the alkoxylation reaction are in particular ethylene oxide and/or propylene oxide, which can be used in any order, or also in a mixture, in the alkoxylation reaction.
Også polytetrametylenglykolpolyeter tilsvarende de ovenfor angitte angivelsene, som er tilgjengelige på i og for seg kjent måte ved kationisk polymerisasjon av tetrahydrofuran, er godt egnet for fremstilling av prepolymerene. Also polytetramethylene glycol polyethers corresponding to the above-mentioned indications, which are available in a manner known per se by cationic polymerization of tetrahydrofuran, are well suited for the production of the prepolymers.
For fremstilling av prepolymerene er videre egnet de hydroksylgruppeholdige poly-karbonatene, tilsvarende de ovenfor angitte betraktningene, som eksempelvis kan fremstilles ved omsetning av enkle dioler av den ovenfor nevnte typen med diarylkarbonater, som eksempelvis difenylkarbonat eller fosgen. For the production of the prepolymers, the hydroxyl group-containing polycarbonates are also suitable, corresponding to the above-mentioned considerations, which can for example be produced by reacting simple diols of the above-mentioned type with diaryl carbonates, such as for example diphenyl carbonate or phosgene.
Egnede for fremstilling av NCO-gruppeholdige prepolymerer er videre polytioeter-polyoler, som eksempelvis kan oppnås ved polykondensasjon av tiodiglykol med seg selv eller med dioler og/eller polyoler av den angitte typen. Suitable for the production of prepolymers containing NCO groups are also polythioether polyols, which can for example be obtained by polycondensation of thiodiglycol with itself or with diols and/or polyols of the specified type.
Videre egner seg polyacetaler, som f.eks. polykondensasjonsprodukter av formaldehyd og dioler, henholdsvis polyoler av den nevnte typen, som kan oppnås under anvendelse av sure katalysatorer som fosforsyre eller p-toluensulfonsyre. Furthermore, polyacetals, such as e.g. polycondensation products of formaldehyde and diols, respectively polyols of the aforementioned type, which can be obtained using acid catalysts such as phosphoric acid or p-toluenesulfonic acid.
Naturligvis kan også blandinger av de som eksempler nevnte hydroksylforbindelsene anvendes for fremstilling av prepolymerene. Naturally, mixtures of the hydroxyl compounds mentioned as examples can also be used to produce the prepolymers.
Spesielt foretrukket anvendes for fremstilling av prepolymerene aromatiske polyisocyanater av den ovenfor nevnte typen, på grunn av den høyere reaktiviteten av de derav fremstilte blokkerte polyisocyanatene A). Aromatic polyisocyanates of the above-mentioned type are particularly preferably used for the production of the prepolymers, due to the higher reactivity of the blocked polyisocyanates A) produced from them.
For fremstilling av de ifølge oppfinnelsen som komponent A) anvendte blokkerte polyisocyanatene er egnede hydrokarbonharpikser oppvisende fenoliske OH-grupper slike av den generelt kjente typen, som eksempelvis er beskrevet i Ullmanns Encyklopådie der technischen Chemie, 4. opplag, bind 12, side 539 til 545, (Verlag Chemie, Weinheim 1976), Kirk-Othmer, Encyclopedia of Chemical Technology, 3. opplag, bind 12, side 852 til 869 (John Wiley & Sons, New York 1980) eller Encyclopedia of Polymer Science and engineering, bind 7, side 758 til 782, (John Wiley & Sons, New York 1987). For the production of the blocked polyisocyanates used according to the invention as component A), suitable hydrocarbon resins exhibiting phenolic OH groups are those of the generally known type, which are for example described in Ullmann's Encyklopådie der technischen Chemie, 4th edition, volume 12, pages 539 to 545 , (Verlag Chemie, Weinheim 1976), Kirk-Othmer, Encyclopedia of Chemical Technology, 3rd edition, Volume 12, pages 852 to 869 (John Wiley & Sons, New York 1980) or Encyclopedia of Polymer Science and Engineering, Volume 7, pages 758 to 782, (John Wiley & Sons, New York 1987).
Eksempler på egnede hydrokarbonharpikser som oppviser fenoliske OH-grupper er kumaron-inden-harpikser, petroleumsharpikser eller terpenharpikser og lignende. Examples of suitable hydrocarbon resins which exhibit phenolic OH groups are coumarone-inden resins, petroleum resins or terpene resins and the like.
Slike hydrokarbonharpikser som oppviser fenoliske OH-grupper fremstilles typisk ved kopolymerisasjon av umettede hydrokarboner av den nedenfor nevnte typen med fenol eller substituerte fenoler i nærvær av sterke syrer eller katalysatorer av Friedel-Crafts-typen. Egnede umettede hydrokarboner for fremstilling av de ifølge oppfinnelsen anvendbare OH-funksjonelle hydrokarbonharpiksene er de ved spaltning av nafta eller gassolje dannede hydrokarbonene, som eksempelvis buten, butadien, penten, piperylen, isopren, cyklopentadien, styren, ct-metylstyren, vinyltoluen, dicyklopentadien, metyl-dicyklopentadien, inden, metylinden. Such hydrocarbon resins exhibiting phenolic OH groups are typically prepared by copolymerization of unsaturated hydrocarbons of the type mentioned below with phenol or substituted phenols in the presence of strong acids or Friedel-Crafts type catalysts. Suitable unsaturated hydrocarbons for the production of the OH-functional hydrocarbon resins applicable according to the invention are the hydrocarbons formed by cracking naphtha or gas oil, such as butene, butadiene, pentene, piperylene, isoprene, cyclopentadiene, styrene, ct-methylstyrene, vinyltoluene, dicyclopentadiene, methyl -dicyclopentadiene, indene, methylindene.
Som umettede hydrokarboner, som er anvendbare for fremstilling av de ifølge oppfinnelsen anvendelige OH-funksjonelle hydrokarbonharpiksene, egner seg dessuten terpenharpikser, som eksempelvis a-pinen, G-pinen, dipenten, D-limonen eller terpentin. Fortrinnsvis anvendbare hydrokarbonharpikser oppviser et hydroksylgruppe-innhold (beregnet som OH, molekylvekt 17) pål,0 til 6,0 vekt-%. Spesielt foretrukket anvendes ved romtemperatur flytende hydrokarbonharpikser med et hydroksylgruppe-innhold på 1,5 til 4,0 vekt-% for fremstilling av komponent A). Terpene resins, such as for example a-pinene, G-pinene, dipene, D-limonene or turpentine, are also suitable as unsaturated hydrocarbons, which can be used for the production of the OH-functional hydrocarbon resins applicable according to the invention. Preferably, usable hydrocarbon resins have a hydroxyl group content (calculated as OH, molecular weight 17) of 1.0 to 6.0% by weight. Liquid hydrocarbon resins with a hydroxyl group content of 1.5 to 4.0% by weight are particularly preferably used at room temperature for the production of component A).
For fremstilling av reaktivesystemene ifølge oppfinnelsen kan de blokkerte polyisocyanatene A) om nødvendig komme til anvendelse i vanlige lakkoppløsningsmidler som eksempelvis etylacetat, butylacetat, metoksypropylacetat, metyletylketon, metyliso-butylketon, toluen, xylen, aromatiske eller (cyklo)alifatiske hydrokarbonblandinger eller hvilke som helst blandinger av slike oppløsningsmidler. For the production of the reactive systems according to the invention, the blocked polyisocyanates A) can, if necessary, be used in common varnish solvents such as ethyl acetate, butyl acetate, methoxypropyl acetate, methyl ethyl ketone, methyl iso-butyl ketone, toluene, xylene, aromatic or (cyclo)aliphatic hydrocarbon mixtures or any mixtures of such solvents.
Ved komponent B) av reaktivsystemene ifølge oppfinnelsen dreier det seg om polyaminer som oppviser minst to primære aminogrupper pr. molekyl og fortrinnsvis har en (midlere) molekylvekt M„ på 60 til 500. Egnede er eksempelvis etylendiamin, 1,2- og 1,3-diaminopropan, 1,4-diaminobutan, 1,6-diaminoheksan, 2,2,4- og/eller 2,4,4-trimetylheksametylendiamin, de isomere xylylendiaminene eller også slike polyaminer som ved siden av minst to primære aminogrupper også oppviser sekundære aminogrupper, som eksempelvis dietylentriamin eller trietylentetramin. In the case of component B) of the reactive systems according to the invention, it concerns polyamines which exhibit at least two primary amino groups per molecule and preferably has an (average) molecular weight M„ of 60 to 500. Suitable examples are ethylenediamine, 1,2- and 1,3-diaminopropane, 1,4-diaminobutane, 1,6-diaminohexane, 2,2,4- and/or 2,4,4-trimethylhexamethylenediamine, the isomeric xylylenediamines or also such polyamines which, in addition to at least two primary amino groups, also exhibit secondary amino groups, such as diethylenetriamine or triethylenetetramine.
Spesielt foretrekkes polyaminer, spesielt diaminer, av det nevnte molekylvektområdet, Particularly preferred are polyamines, especially diamines, of the aforementioned molecular weight range,
som oppviser en eller flere cykloalifatiske ringer. Hertil hører eksempelvis 1,4-diamino-cykloheksan, 4,4'-diaminodicykloheksylmetan, 1,3-diaminocyklopentan, 4,4'-diamino-dicykloheksylsulfon, 4,4'-diaminodicykloheksylpropan-l ,3,4,4'-diaminodicykloheksylpropan-2,2, 3,3'-dimetyl-4,4'-diaminodicykloheksylmetan, 3-aminometyl-3,3,5-tri-metylcykloheksylamin (isoforondiamin) eller teknisk bis-aminometyltricyklodekan, som markedsføres under betegnelsen "TCD-Diamin" fra firma Hoechst AG. which exhibit one or more cycloaliphatic rings. These include, for example, 1,4-diamino-cyclohexane, 4,4'-diaminodicyclohexylmethane, 1,3-diaminocyclopentane, 4,4'-diamino-dicyclohexylsulfone, 4,4'-diaminodicyclohexylpropane-1,3,4,4'-diaminodicyclohexylpropane -2,2,3,3'-dimethyl-4,4'-diaminodicyclohexylmethane, 3-aminomethyl-3,3,5-tri-methylcyclohexylamine (isophoronediamine) or technical bis-aminomethyltricyclodecane, which is marketed under the name "TCD-Diamine" from the company Hoechst AG.
Likeledes anvendbare som komponent B) er addukter, som fremstilles ved omsetning av et overskudd av de nevnte polyaminene med epoksydharpikser av den nedenfor angitte typen. Likewise usable as component B) are adducts, which are produced by reacting an excess of the mentioned polyamines with epoxy resins of the type indicated below.
Videre er også polyamidharpikser egnede som komponent B). Slike polyamidharpikser, hvortil polyaminoamider og polyaminoimidazoliner hører, markedsføres blant annet av Henkel under handelsnavnet "Versamid". Furthermore, polyamide resins are also suitable as component B). Such polyamide resins, to which polyaminoamides and polyaminoimidazolines belong, are marketed, among others, by Henkel under the trade name "Versamid".
Videre anvendbare som komponenter B) er polyeteraminer, som fremstilles ved omsetning av polyeterpolyoler med ammoniakk, og eksempelvis markedsføres av firma Huntsman under handelsnavnet "Jeffamin". Also usable as components B) are polyetheramines, which are produced by reacting polyether polyols with ammonia, and for example marketed by the company Huntsman under the trade name "Jeffamin".
Naturligvis er det også mulig å anvende blandinger av de nevnte polyaminene som komponent B). Naturally, it is also possible to use mixtures of the mentioned polyamines as component B).
Generelt foreligger i reaktivsystemene ifølge oppfinnelsen komponentene A) og B) i slike mengder som tilsvarer et ekvivalent forhold av blokkerte isocyanatgrupper av komponent A) til primære og eventuelt sekundære aminogrupper av komponent B) på 0,8:1 til 1,2:1, fortrinnsvis 0,9:1 til 1,1:1. In general, in the reactive systems according to the invention, components A) and B) are present in such amounts that correspond to an equivalent ratio of blocked isocyanate groups of component A) to primary and possibly secondary amino groups of component B) of 0.8:1 to 1.2:1, preferably 0.9:1 to 1.1:1.
Reaktivsystemene ifølge oppfinnelsen har, sammenlignet med teknikkens stand, uvanlig gunstig forhold mellom lagringsstabilitet og innbrenningstemperatur, hvilket er avhengig av anvendt katalysatorsystem. Følgelig kan f.eks. blandinger fremstilles som ukatalysert ved romtemperatur er bearbeidbare i flere dager, men som imidlertid ved temperaturforhøyelse til 120°C herder i løpet av 20 minutter. Det kan også fremstilles blandinger ved samtidig anvendelse av en katalysator, slik at de ved romtemperatur har en bearbeidelsestid på 3 til 4 timer og er gjennomherdet etter 24 timer. The reactive systems according to the invention have, compared to the state of the art, an unusually favorable relationship between storage stability and burn-in temperature, which is dependent on the catalyst system used. Consequently, e.g. mixtures are produced which, uncatalyzed at room temperature, can be processed for several days, but which, however, harden within 20 minutes when the temperature is increased to 120°C. Mixtures can also be prepared by simultaneously using a catalyst, so that at room temperature they have a processing time of 3 to 4 hours and are fully cured after 24 hours.
Som egnede katalysatorer egner seg fortrinnsvis forbindelser som oppviser basiske nitrogenatomer. Nevnes skal eksempelvis tert.-aminer eller mannich-baser. Spesielt foretrukket anvendes imidlertid amidiner for katalyse. Spesielt foretrukne katalysatorer er hvilke som helst amidinbaser som bærer eventuelt substituerte alkyl-, aralkyl- eller arylrester, hvorved CN-dobbeltbindingen av amidinstrukturen kan være anordnet så vel som del av et åpenkjedet molekyl, som også som bestanddel av et cyklisk eller dicyklisk system, eller også eksocyklisk på et ringsystem, eller hvilke som helst blandinger av slike amidiner. Suitable catalysts are preferably compounds which exhibit basic nitrogen atoms. Mention should be made, for example, of tert-amines or Mannich bases. Particularly preferably, however, amidines are used for catalysis. Particularly preferred catalysts are any amidine bases bearing optionally substituted alkyl, aralkyl or aryl residues, whereby the CN double bond of the amidine structure can be arranged as well as part of an open-chain molecule, as also as a component of a cyclic or dicyclic system, or also exocyclic on a ring system, or any mixtures of such amidines.
Egnede amidinkatalysatorer, hvori CN-dobbeltbindingen foreligger som del av et åpenkjedet molekyl, er eksempelvis N,N-dimetyl-N'-fenylformamidin eller N,N,N'-trimetylformamidin, hvis fremstilling f.eks. er beskrevet i Chem. Ber. 98, 1078 (1965). Som eksempler på egnede amidiner C), hvorved CN-dobbeltbindingen er bestanddel av et cyklisk system, skal her nevnes: i 1-stilling substituerte 2-metyltetrahydropyrimidiner, slik disse eksempelvis kan oppnås ifølge læren i DE-A 2 439 550 ved omsetning av N-monosubstituerte 1,3-propandiaminer med aceteddiksyrederivater, eller monocykliske amidinbaser, slik disse ifølge DE-A 1 078 568 er tilgjengelig ved reaksjon av karba-moylklorider fra sekundære aminer med laktamer. Egnede katalysatorer C), ved hvilke DN-dobbeltbindingen er anordnet eksocyklisk på et ringsystem, er eksempelvis imin N-alkylsubstituerte laktamer, som 2-metylimino-l-metyl-pyrroIidon, hvis fremstilling f.eks. er beskrevet i Chem. Ber. 101,3002 (1968). Suitable amidine catalysts, in which the CN double bond is present as part of an open-chain molecule, are for example N,N-dimethyl-N'-phenylformamidine or N,N,N'-trimethylformamidine, the preparation of which e.g. is described in Chem. Pray. 98, 1078 (1965). As examples of suitable amidines C), whereby the CN double bond is part of a cyclic system, the following shall be mentioned here: 2-methyltetrahydropyrimidines substituted in the 1-position, as these can for example be obtained according to the teachings of DE-A 2 439 550 by reaction of N -monosubstituted 1,3-propanediamines with acetoacetic acid derivatives, or monocyclic amidine bases, as these are available according to DE-A 1 078 568 by reaction of carbamoyl chlorides from secondary amines with lactams. Suitable catalysts C), in which the DN double bond is arranged exocyclically on a ring system, are for example imine N-alkyl substituted lactams, such as 2-methylimino-1-methyl-pyrrolidone, the preparation of which e.g. is described in Chem. Pray. 101,3002 (1968).
Også bicykliske amidiner, slik de f.eks. beskrives i EP-A 662 476, eksempelvis 1,5-diazabicyklo[4.4.0]non-5-en (DBN) er anvendbare ifølge oppfinnelsen. Also bicyclic amidines, as they e.g. are described in EP-A 662 476, for example 1,5-diazabicyclo[4.4.0]non-5-ene (DBN) are usable according to the invention.
Reaktivsystemene ifølge oppfinnelsen kan eventuelt anvendes om trekomponent-systemer og inneholder da som ytterligere komponent C) forbindelser som oppviser oksirangmpper. Egnede forbindelser som oppviser oksirangmpper er epoksydharpikser, som i gjennomsnitt inneholder mer enn én epoksydgruppe pr. molekyl. Eksempler på egnede epoksydharpikser er glycidyletere av flerverdige alkoholer, som f.eks. butandiol, heksandiol, glyserol, hydrert difenylolpropan eller flerverdige fenoler, som f.eks. resorcin, difenylolpropan, difenylolmetan (bisfenol F) eller fenol-aldehyd-kondens-atorer. Det kan også anvendes glycidylestere av flerverdige karboksylsyrer, som heksahydroftalsyre eller dimerisert fettsyre. The reactive systems according to the invention can optionally be used for three-component systems and then contain as an additional component C) compounds which exhibit oxirange mps. Suitable compounds exhibiting oxiranmps are epoxide resins, which on average contain more than one epoxide group per molecule. Examples of suitable epoxy resins are glycidyl ethers of polyhydric alcohols, such as e.g. butanediol, hexanediol, glycerol, hydrogenated diphenylolpropane or polyvalent phenols, such as e.g. resorcinol, diphenylolpropane, diphenylolmethane (bisphenol F) or phenol-aldehyde condensers. Glycidyl esters of polyhydric carboxylic acids, such as hexahydrophthalic acid or dimerized fatty acid, can also be used.
Spesielt foretrukket er anvendelsen av flytende epoksydharpikser på basis av epiklorhydrin og difenylolpropan-2.2 (bisfenol A) med en molekylvekt på 340 til 450. Om ønsket kan med monofunksjonelle epoksydforbindelser viskositeten av blandingene reduseres og derved kan bearbeidelsen forbedres. Eksempler på dette er alifatiske og aromatiske glycidyletere som butylglycidyleter, fenylglycidyleter eller glycidylestere som versatinsyreglycidylester eller epoksyder som styrenoksyd eller 1,2-epoksyd-dodekan. Particularly preferred is the use of liquid epoxy resins based on epichlorohydrin and diphenylolpropane-2.2 (bisphenol A) with a molecular weight of 340 to 450. If desired, the viscosity of the mixtures can be reduced with monofunctional epoxy compounds and thus processing can be improved. Examples of this are aliphatic and aromatic glycidyl ethers such as butyl glycidyl ether, phenyl glycidyl ether or glycidyl esters such as versatic acid glycidyl ester or epoxides such as styrene oxide or 1,2-epoxide-dodecane.
I slike trekomponent-reaktivsystemer ifølge oppfinnelsen foreligger generelt pr. epoksydgmppe av komponent C) 0,4 til 0,9, fortrinnsvis 0,5 til 0,8 primære aminogrupper av komponent B) og 0,02 til 0,5, fortrinnsvis 0,03 til 0,4 blokkerte isocyanatgrupper av komponent A). Slike trekomponent-reaktivsystemer anvendes generelt som romtemperatur-herdende systemer. In such three-component reactive systems according to the invention, there are generally per epoxide group of component C) 0.4 to 0.9, preferably 0.5 to 0.8 primary amino groups of component B) and 0.02 to 0.5, preferably 0.03 to 0.4 blocked isocyanate groups of component A) . Such three-component reactive systems are generally used as room temperature curing systems.
For fremstilling av bruksferdige blandinger kan kombinasjonen av komponentene A), B) og C) ifølge oppfinnelsen suppleres med vanlige hjelpe- og tilsatsmidler, som eksempelvis fyllstoffer, oppløsningsmidler, flythjelpemidler, pigmenter, oppløsnings-midler, reaksjonsakseleratorer eller viskositetsregulerende midler. Eksempelvis skal nevnes reaksjonsakseleratorer som salisylsyre, bis(dimetylaminometyl)fenol eller tris(dimetylaminometyl)fenol, fyllstoffer som sandtyper, steinmel, kiselsyre, asbestmel, kaolin, talkum, metallpulver, tjære, tjæreasfalt, asfalter, korkavfall, polyamider, myknere som eksempelvis ftalsyreester eller andre viskositetsregulerende midler som eksempelvis benzylalkohol. For the production of ready-to-use mixtures, the combination of components A), B) and C) according to the invention can be supplemented with common auxiliaries and additives, such as fillers, solvents, flow aids, pigments, solvents, reaction accelerators or viscosity-regulating agents. Examples include reaction accelerators such as salicylic acid, bis(dimethylaminomethyl)phenol or tris(dimethylaminomethyl)phenol, fillers such as types of sand, stone flour, silicic acid, asbestos flour, kaolin, talc, metal powder, tar, tar asphalt, asphalts, cork waste, polyamides, plasticizers such as phthalic acid ester or other viscosity-regulating agents such as, for example, benzyl alcohol.
Reaktivsystemene ifølge oppfinnelsen egner seg for fremstilling av belegg, klebestoffer, tetningsmasser, støpemasser eller formdeler innenfor alle anvendelsesområder hvor godt vedheng, kjemikaliefasthet, samt høy slag- og støtfasthet, forbundet med god fleksibilitet og elastisitet er påkrevet. Dersom spesielt myke og elastiske materialer er påkrevet inneholder reaktivsystemene fortrinnsvis ingen komponent C). Dersom høyt tverrbundede, kjemikaliebestandige materialer er påkrevet, så inneholder reaktivsystemene bare en liten andel av komponent A), som virker til elastifisering av epoksydharpiksen C). The reactive systems according to the invention are suitable for the production of coatings, adhesives, sealing compounds, molding compounds or molded parts in all areas of application where good adhesion, chemical resistance, as well as high impact and shock resistance, combined with good flexibility and elasticity are required. If particularly soft and elastic materials are required, the reactive systems preferably contain no component C). If highly cross-linked, chemically resistant materials are required, then the reactive systems only contain a small proportion of component A), which acts to elastise the epoxy resin C).
Eksempler Examples
Alle prosentangivelser i eksemplene vedrører, såfremt ikke annet er angitt, vekt. All percentages in the examples relate, unless otherwise stated, to weight.
Eksempel 1 Example 1
1330 g av en polyeterpolyol av OH-tall 42, fremstilt ved samtidig etoksylering og propoksylering (EO/PO-forhold = 2:8) av en 1:2 blanding av propylenglykol og glyserol, prepolymeriseres med 174 g 2,4-diisocyanatotoluen i 5 timer ved 80°C, inntil det teoretiske NCO-innholdet på 2,8 % er nådd. 1330 g of a polyether polyol of OH number 42, produced by simultaneous ethoxylation and propoxylation (EO/PO ratio = 2:8) of a 1:2 mixture of propylene glycol and glycerol, is prepolymerized with 174 g of 2,4-diisocyanatotoluene in 5 hours at 80°C, until the theoretical NCO content of 2.8% is reached.
Deretter tilsetter man 800 g av en handelsvanlig hydrokarbonharpiks med et hydroksylgruppeinnhold på 2,25 % ("Novares LA 700", handelsprodukt fra firma VFT AG, Duisburg), katalyserer med 0,2 g tinn(II)oktoat og omrører inntil ikke lenger fritt isocyanat kan påvises. Den oppnådde blokkerte isocyanatprepolymeren har følgende karakteristiske data: 800 g of a commercially available hydrocarbon resin with a hydroxyl group content of 2.25% ("Novares LA 700", commercial product from the company VFT AG, Duisburg) are then added, catalyzed with 0.2 g of tin(II) octoate and stirred until no longer free isocyanate can be detected. The obtained blocked isocyanate prepolymer has the following characteristic data:
innhold av blokkert NCO: 1,8 % content of blocked NCO: 1.8%
viskositet (23°C): 62.000 mPas viscosity (23°C): 62,000 mPas
233 g av prepolymeren omrøres grundig med 11,9 g 3,3'-dimetyl-4,4'-diaminodicykloheksylmetan. Blandingen har en bearbeidelsestid på 48 timer. Blandingen helles ut i en 233 g of the prepolymer is thoroughly stirred with 11.9 g of 3,3'-dimethyl-4,4'-diaminodicyclohexylmethane. The mixture has a processing time of 48 hours. The mixture is poured into a
sjikttykkelse på 3 mm og herdes ved 20 minutters oppvarming til 120°C. Derved oppnår man en klar, elastisk plast med følgende mekaniske egenskaper: layer thickness of 3 mm and is hardened by heating to 120°C for 20 minutes. This results in a clear, elastic plastic with the following mechanical properties:
Eksempel 2 Example 2
NCO-prepolymeren fremstilles som beskrevet i eksempel 1. Blokkeringsreaksjonen gjennomføres på analog måte, imidlertid anvendes 940 g av en annen handelsvanlig hydrokarbonharpiks med et hydroksylgruppeinnhold på 1,9 % ("Novares LA 300", handelsprodukt fra firma VFT AG, Duisburg). Den oppnådde blokkerte isocyanatprepolymeren har følgende karakteristiske data: 247 g av prepolymeren omrøres grundig med 11,9 g 3,3'-dimetyl-4,4'-diaminodicykloheksylmetan og 2,5 g l,8-diazabicyklo[5.4.0]undec-7-en (DBU). Blandingen helles ut i en sjikttykkelse på 3 mm og herder ved romtemperatur i løpet av 6 timer. Den oppnådde klare, elastiske plasten har følgende mekaniske egenskaper: The NCO prepolymer is prepared as described in example 1. The blocking reaction is carried out in an analogous manner, however, 940 g of another commercially available hydrocarbon resin with a hydroxyl group content of 1.9% ("Novares LA 300", commercial product from the company VFT AG, Duisburg) is used. The obtained blocked isocyanate prepolymer has the following characteristic data: 247 g of the prepolymer is thoroughly stirred with 11.9 g of 3,3'-dimethyl-4,4'-diaminodicyclohexylmethane and 2.5 g of 1,8-diazabicyclo[5.4.0]undec-7 - one (DBU). The mixture is poured in a layer thickness of 3 mm and hardens at room temperature within 6 hours. The resulting clear, elastic plastic has the following mechanical properties:
Eksempel 3 Example 3
425 g av en polyesterdiol av OH-tall 66, fremstilt ved forestring av heksandiol-1,6 og neopentylglykol i molforhold 1:1 med adipinsyre og 500 g av en polyeterdiol fremstilt ved propoksylering av propylenglykol, OH-tall 56 og 4,5 g trimetylolpropan prepolymeriseres med 174 g av en teknisk 80:20 blanding av 2,4-diisocyanatotoluen og 2,6-diisocyanatotoluen ved 70°C, inntil det teoretiske NCO-innholdet på 3,1 % er nådd. 425 g of a polyester diol of OH number 66, produced by esterification of hexanediol-1,6 and neopentyl glycol in a 1:1 molar ratio with adipic acid and 500 g of a polyether diol produced by propoxylation of propylene glycol, OH number 56 and 4.5 g Trimethylolpropane is prepolymerized with 174 g of a technical 80:20 mixture of 2,4-diisocyanatotoluene and 2,6-diisocyanatotoluene at 70°C, until the theoretical NCO content of 3.1% is reached.
Deretter tilsetter man 440 g av en handelsvanlig hydrokarbonharpiks med et hydroksylgruppeinnhold på 3,9 % ("Necirés EPX-LC", handelsprodukt fra firma Nevcin Polymers B.V., Uithoorn, Holland), katalyserer med 0,2 g tinn(II)oktoat og omrører 10 timer ved 60°C. Etter denne tiden kan i IR-spekteret ikke lenger fritt isocyanat påvises. Den oppnådde blokkerte isocyanatprepolymeren oppløses 95 %-ig i metoksypropylacetat og har da følgende karakteristiske data: 179 g av prepolymeren omrøres grundig med 11,9 g 3,3'-dimetyl-4,4'-diaminodicykloheksylmetan. Blandingen har en bearbeidelsestid på 48 timer. Blandingen påføres i en sjikttykkelse på 0,2 mm på en glassplate og utherdes ved 20 minutters oppvarming til 120°C. Derved oppnås en klar, høyelastisk polymerfilm med følgende egenskaper: 440 g of a commercially available hydrocarbon resin with a hydroxyl group content of 3.9% ("Necirés EPX-LC", commercial product from the company Nevcin Polymers B.V., Uithoorn, Holland) are then added, catalyzed with 0.2 g of tin(II) octoate and stirred 10 hours at 60°C. After this time, free isocyanate can no longer be detected in the IR spectrum. The obtained blocked isocyanate prepolymer is 95% dissolved in methoxypropyl acetate and then has the following characteristic data: 179 g of the prepolymer is thoroughly stirred with 11.9 g of 3,3'-dimethyl-4,4'-diaminodicyclohexylmethane. The mixture has a processing time of 48 hours. The mixture is applied in a layer thickness of 0.2 mm on a glass plate and cured by heating to 120°C for 20 minutes. This results in a clear, highly elastic polymer film with the following properties:
Eksempel 4 Example 4
3000 g av en polyeterpolyol av OH-tall 48, fremstilt ved propoksylering av trimetylolpropan, oppvarmes med 1400 g 2,4-diisocyanatotoluen i 5 timer under omrøring til 70°C. Deretter fjernes overskuddet av diisocyanat ved vakuum-tynnsjiktdestillasjon ved 140°C/0,2 mbar. Det oppstår en prepolymer som oppviser isocyanatendegrupper med et HCO-innhold på 3,2 %. 3000 g of a polyether polyol of OH number 48, produced by propoxylation of trimethylolpropane, is heated with 1400 g of 2,4-diisocyanatotoluene for 5 hours with stirring to 70°C. The excess of diisocyanate is then removed by vacuum thin-layer distillation at 140°C/0.2 mbar. A prepolymer is produced which exhibits isocyanate end groups with an HCO content of 3.2%.
Til 1310 g av denne prepolymeren tilsettes 800 g av en handelsvanlig hydrokarbonharpiks med et hydroksylgruppeinnhold på 2,25 % ("Novares LA 700", handelsprodukt fra firma VFT AG, Duisburg) og 0,2 g tinn(II)oktoat. Det omrøres i 10 timer ved 60°C. Etter denne tiden kan i IR-spekteret ikke lenger fritt isocyanat påvises. Den oppnådde blokkerte isocyanatprepolymeren har følgende karakteristiske data: 210 g av prepolymeren omrøres grundig med 8,5 g isoforondiamin. Blandingen uthelles i en sjikttrykkelse på 3 mm og utherdes ved 20 minutters oppvarming til 120°C. Man oppnår derved en klar, elastisk plast med følgende mekaniske egenskaper: To 1310 g of this prepolymer are added 800 g of a commercially available hydrocarbon resin with a hydroxyl group content of 2.25% ("Novares LA 700", commercial product from the company VFT AG, Duisburg) and 0.2 g of tin (II) octoate. It is stirred for 10 hours at 60°C. After this time, free isocyanate can no longer be detected in the IR spectrum. The obtained blocked isocyanate prepolymer has the following characteristic data: 210 g of the prepolymer are thoroughly stirred with 8.5 g of isophoronediamine. The mixture is poured into a layer pressure of 3 mm and cured by heating to 120°C for 20 minutes. This results in a clear, elastic plastic with the following mechanical properties:
Eksempel 5 Example 5
75 g av prepolymeren fra eksempel 2 blandes med 25 g av en standard-epoksydharpiks ("Epikote 828", handelsprodukt fra firma Shell, epoksydekvivalentvekt 190) og 8,5 g isoforondiamin. Blandingen herder over natten ved romtemperatur. Den oppnådde, lett opake, seig-elastiske plasten har en Shore A-hårdhet på 84 og en Shore D-hårdhet på 27. 75 g of the prepolymer from example 2 is mixed with 25 g of a standard epoxy resin ("Epikote 828", commercial product from the company Shell, epoxy equivalent weight 190) and 8.5 g of isophoronediamine. The mixture hardens overnight at room temperature. The resulting slightly opaque, tough-elastic plastic has a Shore A hardness of 84 and a Shore D hardness of 27.
Eksempel 6 Example 6
50 g av prepolymeren fra eksempel 2 blandes med 50 g av en standard-epoksydharpiks ("Epikote 828", handelsprodukt fra firma Shell, epoksydekvivalentvekt 190) og 13 g isoforondiamin. Blandingen herder over natten ved romtemperatur. Den oppnådde opake, slagseige plasten har en Shore D-hårdhet på 72. 50 g of the prepolymer from example 2 is mixed with 50 g of a standard epoxy resin ("Epikote 828", commercial product from the company Shell, epoxy equivalent weight 190) and 13 g of isophoronediamine. The mixture hardens overnight at room temperature. The resulting opaque, impact-resistant plastic has a Shore D hardness of 72.
Eksempel 7 Example 7
25 g av prepolymeren fra eksempel 2 blandes med 75 g av en standard-epoksydharpiks ("Epikote 828", handelsprodukt fra firma Shell, epoksydekvivalentvekt 190) og 55 g isoforondiamin. Blandingen herder i løpet av 5 timer ved romtemperatur. Den oppnådde opake, sprø plasten har en Shore D-hårdhet på 80. 25 g of the prepolymer from example 2 is mixed with 75 g of a standard epoxy resin ("Epikote 828", commercial product from the company Shell, epoxy equivalent weight 190) and 55 g of isophoronediamine. The mixture hardens within 5 hours at room temperature. The resulting opaque, brittle plastic has a Shore D hardness of 80.
Eksempel 8 Example 8
50 g av prepolymeren fra eksempel 2 blandes med 3,2 g av et handelsvanlig polyamin-addukt-herdemiddel på basis av isoforondiamin/epoksydharpiks med en aminverdi på 6,5 ekvivalenter/kg (Hårter HY 847", handelsprodukt fra firma Ciba Specialty Chemicals). Blandingen herdes ved 6 timers oppvarming til 60°C. Derved oppnås en transparent, høyelastisk plast av en Shore A-hårdhet på 20. 50 g of the prepolymer from example 2 is mixed with 3.2 g of a commercial polyamine adduct curing agent based on isophoronediamine/epoxide resin with an amine value of 6.5 equivalents/kg (Hårter HY 847", commercial product from the company Ciba Specialty Chemicals) . The mixture is hardened by heating for 6 hours at 60° C. This results in a transparent, highly elastic plastic with a Shore A hardness of 20.
Eksempel 9 Example 9
1330 g av polyeterpolyolen fra eksempel 1 prepolymeriseres med 222 g isoforondiisocyanat i 20 timer ved 100°C, inntil det teoretiske NCO-innholdet på 2,8 % er nådd. Deretter tilsetter man 940 g av en handelsvanlig hydrokarbonharpiks fra eksempel 2, katalyserer med 0,4 g tinn(U)oktoat og omrører i 10 timer ved 80°C. Etter denne tiden kan det i IR-spekteret ikke lenger påvises fritt isocyanat. Den oppnådde blokkerte isocyanatprepolymeren har følgende karakteristiske data: 1330 g of the polyether polyol from example 1 is prepolymerized with 222 g of isophorone diisocyanate for 20 hours at 100°C, until the theoretical NCO content of 2.8% is reached. 940 g of a commercial hydrocarbon resin from example 2 is then added, catalyzed with 0.4 g of tin (U) octoate and stirred for 10 hours at 80°C. After this time, free isocyanate can no longer be detected in the IR spectrum. The obtained blocked isocyanate prepolymer has the following characteristic data:
247 g av prepolymeren omrøres grundig med 11,9 g 3,3'-dimetyl-4,4'-diaminodicykloheksylmetan. Blandingen uthelles i en sjikttykkelse på 3 mm og herdes ved 90 minutters oppvarming til 120°C. Det oppnås derved en transparent, høyelastisk plast av en Shore A-hårdhet på 22. 247 g of the prepolymer is thoroughly stirred with 11.9 g of 3,3'-dimethyl-4,4'-diaminodicyclohexylmethane. The mixture is poured into a layer thickness of 3 mm and hardened by heating to 120°C for 90 minutes. This results in a transparent, highly elastic plastic with a Shore A hardness of 22.
Eksempel 10 Example 10
425 g av polyesterdiolen fra eksempel 3, 500 g av polyeterdiolen fra eksempel 3 og 4,5 g trimetylolpropan prepolymeriseres med 222 g isoforondiisocyanat ved 100°C, inntil det teoretiske NCO-innholdet på 3,3 % er nådd. 425 g of the polyester diol from example 3, 500 g of the polyether diol from example 3 and 4.5 g of trimethylolpropane are prepolymerized with 222 g of isophorone diisocyanate at 100°C, until the theoretical NCO content of 3.3% is reached.
Deretter tilsetter man 940 g av en handelsvanlig hydrokarbonharpiks fra eksempel 2, katalyserer med 0,4 g tinn(II)oktoat og omrører i 10 timer ved 80°C. Etter denne tiden kan det i IR-spekteret ikke lenger påvises fritt isocyanat. Den oppnådde blokkerte isocyanatprepolymeren oppløses 95 %-ig i metoksypropylacetat og har da følgende karakteristiske data: 940 g of a commercially available hydrocarbon resin from example 2 is then added, catalyzed with 0.4 g of tin(II) octoate and stirred for 10 hours at 80°C. After this time, free isocyanate can no longer be detected in the IR spectrum. The obtained blocked isocyanate prepolymer dissolves 95% in methoxypropyl acetate and then has the following characteristic data:
247 g av prepolymeren utrøres grundig med 10,5 g 4,4'-diaminodicykloheksylmetan. Blandingen helles ut i en sjikttykkelse på 3 mm og herdes ved 90 minutters oppvarming til 120°C. Derved oppnås en transparent, høyelastisk plast av en Shore A-hårdhet på 18. 247 g of the prepolymer is thoroughly stirred with 10.5 g of 4,4'-diaminodicyclohexylmethane. The mixture is poured out in a layer thickness of 3 mm and hardened by heating to 120°C for 90 minutes. This results in a transparent, highly elastic plastic with a Shore A hardness of 18.
Eksempel 11 Example 11
Sammenligningseksempel relativt til DE-A 2 152 606 - ikke ifølge oppfinnelsen. Comparative example relative to DE-A 2 152 606 - not according to the invention.
Til 1504 g av NCO-prepolymeren fra eksempel 1 tilsettes 245 g av en teknisk nonylfenol-isomerblanding. Etter katalyse med 0,2 g tinn(II)oktoat etteromrøres i 10 timer ved 60°C. Etter denne tiden kan det i IR-spekteret ikke lenger påvises fritt isocyanat. Den oppnådde blokkerte isocyanatprepolymeren har følgende karakteristiske data: 175 g av prepolymeren omrøres grundig med 11,9 g 3,3'-dimetyl-4,4'-diaminodicykloheksylmetan. Blandingen har en bearbeidelsestid på bare 6 timer. Etter fullstendig utherding oppnår man en klar, elastisk plast med følgende mekaniske egenskaper: To 1504 g of the NCO prepolymer from example 1, 245 g of a technical nonylphenol isomer mixture is added. After catalysis with 0.2 g of tin(II) octoate, the mixture is stirred for 10 hours at 60°C. After this time, free isocyanate can no longer be detected in the IR spectrum. The obtained blocked isocyanate prepolymer has the following characteristic data: 175 g of the prepolymer is thoroughly stirred with 11.9 g of 3,3'-dimethyl-4,4'-diaminodicyclohexylmethane. The mixture has a processing time of only 6 hours. After complete curing, a clear, elastic plastic with the following mechanical properties is obtained:
Claims (6)
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DE19816570A DE19816570A1 (en) | 1998-04-15 | 1998-04-15 | Reactive systems and their use for the production of coatings, adhesives, sealants, casting compounds or molded parts |
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US (1) | US6060574A (en) |
EP (1) | EP0950675B1 (en) |
JP (1) | JP4442947B2 (en) |
KR (1) | KR100582155B1 (en) |
AT (1) | ATE279460T1 (en) |
CA (1) | CA2268432C (en) |
DE (2) | DE19816570A1 (en) |
DK (1) | DK0950675T3 (en) |
ES (1) | ES2230761T3 (en) |
NO (1) | NO319323B1 (en) |
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DE19935329A1 (en) | 1999-07-28 | 2001-02-01 | Bayer Ag | Polyamines containing urea groups, processes for their preparation and their use as hardeners for epoxy resins |
DE19935325A1 (en) | 1999-07-28 | 2001-02-01 | Bayer Ag | Solvent-free, room temperature curing reactive systems and their use for the production of adhesives, sealants, casting compounds, molded parts or coatings |
WO2001083577A2 (en) * | 2000-05-03 | 2001-11-08 | Dow Global Technologies Inc. | Process for producing polyurethane elastomer |
DE10055559A1 (en) * | 2000-11-09 | 2002-05-29 | Henkel Kgaa | UV-resistant flocking adhesive for polymer substrates |
JP4536249B2 (en) * | 2000-11-28 | 2010-09-01 | 花王株式会社 | Thermosetting urethane composition |
US20030212236A1 (en) * | 2001-05-01 | 2003-11-13 | Luigi Pellacani | Process for producing polyurethane elastomer |
DE10226926A1 (en) * | 2002-06-17 | 2004-02-05 | Bayer Ag | Blocked polyisocyanates |
US20040079477A1 (en) * | 2002-10-25 | 2004-04-29 | Lear Corporation | Method of making an interior trim part |
DE10254376A1 (en) * | 2002-11-15 | 2004-05-27 | Bayer Ag | Preparation of blocked polyurethane prepolymers by reaction of di- or polyisocyanates with polyetherpolyols useful in the preparation of adhesives, sealants, casting compositions, composites, shaped parts, and coatings |
DE10260299A1 (en) * | 2002-12-20 | 2004-07-01 | Bayer Ag | Reactive systems, their manufacture and their use |
DE10316396A1 (en) * | 2003-04-10 | 2004-11-04 | Bayer Materialscience Ag | Phenolic-blocked polyurethane prepolymers |
US7625963B2 (en) * | 2007-01-25 | 2009-12-01 | Henkel Ag & Co. Kgaa | Reactive hot melt adhesive with bituminous additive |
FR2981648B1 (en) * | 2011-10-20 | 2014-12-26 | Soprema | POLYMERIZABLE PLASTICIZER, LIQUID POLYURETHANE RESIN COMPOSITION COMPRISING SAID PLASTICIZER AND USES THEREOF |
FR2981649B1 (en) | 2011-10-20 | 2013-11-22 | Soprema | MASK POLYISOCYANATE AND USES THEREOF |
WO2013057439A2 (en) | 2011-10-20 | 2013-04-25 | Soprema | Stable, ready-to-use liquid polyurethane resin composition and uses thereof |
DE102012201873B4 (en) | 2012-02-08 | 2016-03-10 | Franken Systems Gmbh | Method of building waterproofing by means of fabric-coated coating |
BR112014031189B1 (en) * | 2012-06-26 | 2021-01-12 | Dow Global Technologies Llc | two-component polyurethane adhesive and process for bonding two substrates |
EP3009461A1 (en) | 2014-10-13 | 2016-04-20 | Sika Technology AG | Polyester prepolymers as a toughener in epoxy formulations |
BR112020011726A2 (en) * | 2017-12-19 | 2020-11-17 | Sika Technology Ag | use of strength enhancers to increase the maximum linear expansion of epoxy resin compositions for single component heat curing |
JP7119991B2 (en) * | 2018-12-27 | 2022-08-17 | 株式会社デンソー | Curable composition and electronic device |
JP2021084936A (en) * | 2019-11-26 | 2021-06-03 | Dic株式会社 | Curable composition, cured product and adhesive |
JP2021102701A (en) * | 2019-12-25 | 2021-07-15 | Dic株式会社 | Curable composition, cured product and adhesive |
EP3892659A1 (en) | 2020-04-08 | 2021-10-13 | Covestro Deutschland AG | Low viscosity isocyanate prepolymers blocked with phenols obtainable from cashew nut shell oil, method for their preparation and their use |
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DE1644813A1 (en) * | 1967-10-06 | 1971-01-21 | Bayer Ag | Manufacture of thermally hardening coatings and manufacture of stoving enamels |
DE2131299C3 (en) * | 1971-06-24 | 1981-04-23 | Bayer Ag, 5090 Leverkusen | Mixtures curable by the action of heat and processes for the production of moldings from these mixtures |
GB1420336A (en) * | 1972-09-18 | 1976-01-07 | Ciba Geigy Ag | Method for bonding surfaces together |
BE790295A (en) * | 1971-10-22 | 1973-04-19 | Bayer Ag | ELASTIFIED PLASTICS |
DE3242782A1 (en) * | 1982-11-19 | 1984-05-24 | Rütgerswerke AG, 6000 Frankfurt | PHENOL-MODIFIED HYDROCARBON RESINS WITH A HIGH OH NUMBER AND METHOD FOR THE PRODUCTION AND USE THEREOF |
US4482661A (en) * | 1983-07-14 | 1984-11-13 | The Valspar Corporation | Aluminized epoxy-urethane coating |
DE3922767A1 (en) * | 1989-07-11 | 1991-01-17 | Bayer Ag | HEAT-CREAMABLE MIXTURES AND THEIR USE FOR THE PRODUCTION OF COATINGS ON HEAT-RESISTANT SUBSTRATES |
FR2664284B1 (en) * | 1990-07-05 | 1994-07-08 | Ceca Sa | MODIFIED TACKIFYING RESINS AND RELATED PRODUCTS FOR HOT MOISTURE CROSS-LINKABLE ADHESIVES; THERMOFUSIBLE ADHESIVES INCORPORATING THEM AND THEIR APPLICATIONS. |
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- 1999-04-03 EP EP99106759A patent/EP0950675B1/en not_active Expired - Lifetime
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CA2268432C (en) | 2009-03-31 |
ES2230761T3 (en) | 2005-05-01 |
NO991766L (en) | 1999-10-18 |
NO991766D0 (en) | 1999-04-14 |
JP4442947B2 (en) | 2010-03-31 |
DK0950675T3 (en) | 2005-02-14 |
EP0950675B1 (en) | 2004-10-13 |
ATE279460T1 (en) | 2004-10-15 |
DE59910793D1 (en) | 2004-11-18 |
CA2268432A1 (en) | 1999-10-15 |
KR100582155B1 (en) | 2006-05-23 |
JPH11322882A (en) | 1999-11-26 |
KR19990083173A (en) | 1999-11-25 |
US6060574A (en) | 2000-05-09 |
EP0950675A1 (en) | 1999-10-20 |
DE19816570A1 (en) | 1999-10-21 |
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